Yolk sac tumors (YSTs) are rare germ-cell malignancies that usually develop in the gonads. Similarly, gastric-type adenocarcinoma of the endocervix (GAS) is a rare kind of gynecological cancer that has piqued interest due to its distinctive clinical and pathological features. These two malignancies in a single patient present a unique and challenging scenario. Here, we present the case of a 33-year-old female who presented with postcoital bleeding and was diagnosed with atypical glandular proliferation consistent with GAS. Interestingly, this patient had a history of a YST treated with left salpingo-oophorectomy and chemoradiation in the Philippines five years prior. A follow-up ultrasound report in the Philippines five months after treatment showed no evidence of residual disease. This case report aims to understand the predisposing factors of these neoplasms and asks if there is a link between them, which is necessary for tailoring surveillance, appropriate therapeutic approaches, and improving patient outcomes.